Sodium Bicarbonate → HCID 178433840, compound

HRID 384330Notes

Reaction equation

HRID 384330 reaction equation
Br.[NH2:2][C:3]1[C:4]([OH:17])=[C:5]([C:9]2[S:13][C:12]([C:14]([OH:16])=[O:15])=[CH:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1.[N:18]([O-])=O.[Na+].[CH3:22][C:23]1([CH3:39])[C:31]2[C:26](=[CH:27][CH:28]=[C:29]([N:32]3[C:36](=[O:37])[CH2:35][C:34]([CH3:38])=[N:33]3)[CH:30]=2)[CH2:25][CH2:24]1.C(=O)(O)[O-].[Na+]>Cl>[CH3:22][C:23]1([CH3:39])[C:31]2[C:26](=[CH:27][CH:28]=[C:29]([N:32]3[C:36](=[O:37])[C:35](=[N:18][NH:2][C:3]4[C:4]([OH:17])=[C:5]([C:9]5[S:13][C:12]([C:14]([OH:16])=[O:15])=[CH:11][CH:10]=5)[CH:6]=[CH:7][CH:8]=4)[C:34]([CH3:38])=[N:33]3)[CH:30]=2)[CH2:25][CH2:24]1

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 23668193Sodium NitriteHCID 510369942-(3,3-Dimethyl-indan-5-yl)-5-methyl-2,4-dihydro-pyrazol-3-oneHCID 574838145-(3-Amino-2-hydroxy-phenyl)-thiophene-2-carboxylic acid hydrobromide

Product 1

HCID 178433840HCID 178433840, compoundYield 15.9%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

5-(3-Amino-2-hydroxy-phenyl)-thiophene-2-carboxylic acid 12c (171 mg, 0.62 mmol) was dissolved in 3 mL of hydrochloric acid (1 N) upon cooling by an ice-water bath, followed by dropwise addition of 1 mL of aqueous sodium nitrite (47 mg, 0.68 mmol). After the mixture was stirred for 20 minutes, 2-(3,3-dimethyl-indan-5-yl)-5-methyl-2,4-dihydro-pyrazol-3-one 8i (150 mg, 0.62 mmol) was added. The mixture was adjusted to pH 8-9 by batch addition of aqueous sodium bicarbonate (781 mg, 9.3 mmol). The generated bubbles were quenched with 2 mL of ethanol and the mixture was warmed up to room temperature and stirred overnight. The reaction was monitored by TLC until the disappearance of the starting materials. The mixture was filtered and the filter cake was dissolved in 20 mL of water. The mixture was adjusted to pH 3˜4 with concentrated hydrochloric acid, filtered and dried. The crude product was purified by HPLC to obtain the title compound 5-(3-{N′-[1-(3,3-dimethyl-indan-5-yl)-3-methyl-5-oxo-1,5-dihydro-pyrazol-4-ylidene]-hydrazino}-2-hydroxy-phenyl)-thiophene-2-carboxylic acid 12 (48 mg, yield 15.9%) as an orange solid.

Workup

  1. temperatureupon cooling by an ice-water bath
  2. customThe generated bubbles were quenched with 2 mL of ethanol
  3. stirringstirred overnight
  4. filtrationThe mixture was filtered
  5. dissolutionthe filter cake was dissolved in 20 mL of water
  6. filtrationfiltered
  7. customdried
  8. customThe crude product was purified by HPLC

Sources & evidence

ORD record
ord-a3c3136de4fc4a35b5fe0a6e753154da
Source dataset
uspto-grants-2013_02
Patent number
US08367710B2

Reaction notes

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